A new guard of millennial tailors is reinventing the fusty art of bespoke menswear, and removing the intimidation factor

WHO BUYS custom suits these days? Joseph Leli, a 48-year-old regional manager for a Napa winery, used to believe only high-level executives kept tailors on speed dial. But then he was tipped off to BLVDier, a “made-to-measure atelier” that opened in Chicago’s trendy Fulton Market District in 2015. “Right off the bat it was a different experience than what I thought, in a positive way,” said Mr. Leli. He was greeted with an espresso by BLVDier’s owner Zach Uttich, 33, who chatted easily with Mr. Leli about upgrading from his off-the-rack Hugo Boss suits. With the intimidation factor removed, Mr. Leli happily joined the...